Acetic Acid → HCID 24854970, compound

HRID 913072Notes

Reaction equation

HRID 913072 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:7][N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[CH3:2].[CH2:20]([C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)[CH3:21].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([CH2:20][CH3:21])=[CH:23][CH:24]=2)[CH2:10][CH2:9]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 115044-EthylanilineHCID 5003444Sodium cyanoborohydrideHCID 59383088HCID 59383088, compound2×

Product 1

HCID 24854970HCID 24854970, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
85 °C

Procedure

A solution of 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-one (94.8 mg, 0.36 mmol, 1.2 equiv; intermediate C1) and 4-ethyl-phenylamine (36.4 mg, 0.30 mmol, 1.0 equiv; commercially available) in ethanol (2 mL) and acetic acid (0.38 mL) was heated to 85° C. After 2 h, sodium cyanoborohydride (22.6 mg, 0.36 mmol, 1.2 equiv), dissolved in ethanol (1 mL), was added and the mixture stirred at 85° C. over night. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 17.2 mg (16%) of the title compound. MS (ISP): 369.4 [M+H]+.

Workup

  1. additionwas added
  2. customRemoval of the solvent
  3. customunder reduced pressure and purification by preparative HPLC on reversed phase
  4. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-0fd44062392941c0bc892dfc31c46a48
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

Loading…